Methyl iodide → HCID 12917664, compound

HRID 1660450Notes

Reaction equation

HRID 1660450 reaction equation
[CH3:1][S:2][CH:3]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:23])=[CH:10][CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH3:26]I.[Cl-].[NH4+]>CN(C)C=O>[CH3:1][S:2][C:3]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:23])=[CH:12][CH:13]=1)([CH3:26])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 20556709HCID 20556709, compound

Product 1

HCID 12917664HCID 12917664, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Anhydrous dimethylformamide (7 ml) was added to 256 mg of methyl α-methylthio[p-(1-oxo-2-isoindolinyl)phenyl]acetate. With ice cooling and stirring, 35 mg (65% content) of sodium hydride was added. The mixture was stirred for 10 minutes at room temperature and again cooled with ice. Methyl iodide (0.1 ml) was added, and the mixture was stirred for 5 minutes. Addition of an aqueous solution of ammonium chloride (100 mg/30 ml) resulted in the precipitation of colorless crystals. The crystals were collected by filtration, washed with 20 ml of water and then with 10 ml of n-hexane, and dried to afford 191 mg of methyl α-methylthio-α-[p-(1-oxo-2-isoindolinyl)phenyl]propionate. The filtrate and the washing were combined and extracted three times with 20 ml of methylene chloride. The extract was washed with 10 ml of water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with 10 ml of n-hexane to afford 39 mg of methyl α-methylthio-α-[p-(1-oxo-2-indolinyl)phenyl]propionate. The total amount of the product was 230 mg (yield 86%).

Workup

  1. stirringThe mixture was stirred for 10 minutes at room temperature
  2. temperatureagain cooled with ice
  3. stirringthe mixture was stirred for 5 minutes
  4. customresulted in the precipitation of colorless crystals
  5. filtrationThe crystals were collected by filtration
  6. washwashed with 20 ml of water
  7. dry with materialwith 10 ml of n-hexane, and dried

Sources & evidence

ORD record
ord-ff9baaa975a041c5a9bae62e2b13381f
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

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